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A mere 12 miles from the bustling heart of Center City, is Philadelphia’s Urban Enclave of Chestnut Hill. For cyclists, this stunning garden neighborhood is easily within reach. This historic neighborhood with cobblestone streets offers fantastic dining, boutique shops, antique stores, the Woodmere Art Museum, and the Official Arboretum of the Commonwealth, Morris Arboretum.

Getting to Chestnut Hill by Bicycle

The bicycle route I’ve put together begins at the Art Museum of Philadelphia and will take you along some of Philadelphia’s amazing bike paths and through the parks and natural areas for which Philadelphia is known.

Indego bikeshare kiosk
By Tyree303 – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=41485821

Where to Rent a Bike Near Center City

Pick up a bike share from Indego at the Philadelphia Art Museum. The kiosk is at the base of the famous Rocky Steps and statue, so be sure to snap a picture with Rocky or record a video of you dashing up the steps.  If you decide to use the bike share, be aware that there are no kiosks in Chestnut Hill. Additional nearby rental options include Wheel Fun Rentals at Boathouse Row or Fairmount Bicycles.

Biking Fairmount Park and Boathouse Row

From the Art Museum, you can opt to ride either side of the river. Ride the west side along MLK Drive or the east side on Kelly Drive. Both routes will take you through Fairmount Park and past Philadelphia’s famous Boathouse Row. For the best view of colorful Boathouse Row, you must be on the west side which provides panoramic views of the Schuylkill River and the boathouse.   

Philadelphia Art Museum Rocky Steps
Philadelphia Art Museum, Photo Credit: Samuel Borges Photography

From MLK Drive, cross the Falls Bridge, an old steel bridge spanning the river. Those on Kelly Drive will not cross but you can stop for photos. From the bridge pick up Ridge Avenue and take that to the Wissahickon Trail. You’ll see the trail after crossing Lincoln Drive and Wissahickon Creek (the trail is on the left).

Philadelphia's Boathouse Row
Boathouse Row, Photo Credit: Getty Images

Cycling the Wissahickon Trail

The Wissahickon Trail provides a scenic ride into Wissahickon Valley Park, but you will only be on the path for under a mile and a half. You’ll be sticking to the paved and gravel bike trails but Wissahickon Valley Park is known in the Philadelphia area for its challenging, rocky, mountain biking trails. The path follows the creek and Lincoln Avenue.

Riding Forbidden Drive

After crossing the Henry Avenue Bridge, you will make a left onto Forbidden Drive, whose name is derived from the protests that led to a prohibition against cars.  Just past the bridge is Lovers Leap. Legend has it that a native American couple plunged to their death from the stone outcropping over a Romeo and Juliet-type family dispute.

When you make the turn onto Forbidden Drive watch for Ten Box, a former guard station and a scenic spot for pictures. Ten Box gets its name from the system of phone boxes that once ran along Forbidden Drive. The box at the guard station was the tenth in the series.

Wissahickon Valley Park, Philadelphia PA
Wissahickon Valley Park, Photo Credit: Mark Henninger, Getty Images

For about 2 miles, Forbidden Drive winds through Wissahickon Valley Park, a more than 2000-acre wooded area surrounding Wissahickon Creek. The park is a National Natural Landmark and offers plenty of picturesque places along the way.

At the Valley Green Inn, a historic inn and popular dining spot, you will cross the creek and onto Valley Green Road. From here you will be riding on public streets. But it’s only for a few miles. Nevertheless, use caution!  

Dogwood tree and historic building in Chestnut Hill PA

Remain on Valley Green Road for about 3/4 of a mile before making a left on Lincoln Drive where you will remain for only a block. At this point, make a right onto West Willow Grove Avenue and take that for .2 miles to Germantown Avenue, the heart of Chestnut Hill.

Depending on the type of bike you are riding you may need to dismount and continue exploring on foot. Germantown Ave and a few other thoroughfares still have the original cobblestone streets.

Azaleas and stonework in front of a residence in Chestnut Hill PA

Spend the Day in Chestnut Hill

A highlight of the area is the Morris Arboretum, a testament to the legacy of the Morris siblings, who transformed their summer retreat into a living museum of exotic plants and classical art. This 92-acre wonder showcases an impressive array of trees, some amongst the oldest in the region, and plays host to vibrant seasonal and annual exhibits, including the much-anticipated Japanese Cherry Blossom Festival.

Beyond the arboretum, Chestnut Hill’s charm extends to its neighborhood streets, lined with historic homes and amazing gardens surrounding them. The Historic District is a treasure trove of architecture and horticulture and is listed on the National Register of Historic Places

Couple walking along the sidewalk among the shops in in Chestnut Hill PA

Chestnut Hill is a hotbed for gourmet dining, unique shopping, and art, particularly at the Woodmere Art Museum. For those seeking a leisurely brunch, the local café, Cake, set in a former greenhouse, offers a delightful menu in a bright, inviting atmosphere.

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